Sodium Iodide → HCID 54023975, compound

HRID 1825744Notes

Reaction equation

HRID 1825744 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[H-].[Na+].ClCO[CH2:17][CH2:18][O:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[I-].[Na+].CN(C)[CH:32]=[O:33]>O>[C:20]([O:19][CH:18]([O:33][CH2:32][C:2]1[NH:1][C:9]2[C:4]([C:3]=1[CH:10]=[O:11])=[CH:5][CH:6]=[CH:7][N:8]=2)[CH3:17])(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6228Dimethylformamide3×HCID 24758Sodium hydrideHCID 27245002-(Chloromethoxy)ethyl benzoateHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 54023975HCID 54023975, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7-azaindole-3-carboxaldehyde (2 g, 13.7 mmol) in dry N,N-dimethylformamide (30 ml) was added dropwise, under nitrogen atmosphere, to a stirring suspension of 60% sodium hydride (oil dispersion) (0.6 g, 15 mmol) in dry N,N-dimethylformamide (10 ml) keeping the temperature between 5–10° C. (ice-water bath). After addition was completed, stirring was continued at the same temperature for 30 min. Then a solution of benzoyloxyethyl chloromethyl ether (3.8 g, 15 mmol) in dry N,N-dimethylformamide (40 ml) was added dropwise. After addition was complete, a catalytic amount of sodium iodide was added, and the temperature was allowed to rise to room temperature. The reaction mixture was allowed to stand at room temperature under nitrogen for 6 days, with intermittent stirring. Then water (100 ml) was added, and the mixture extracted with dichloromethane (3×100 ml). The organic phase was washed with water (100 ml), dried over anhydrous magnesium sulfate, filtered and the solvent removed under reduced pressure to give an oil (4.4 g, 99%), which was used without further purification.

Workup

  1. custombetween 5–10° C.
  2. additionAfter addition
  3. additionAfter addition
  4. customto rise to room temperature
  5. waitto stand at room temperature under nitrogen for 6 days, with intermittent stirring
  6. extractionthe mixture extracted with dichloromethane (3×100 ml)
  7. washThe organic phase was washed with water (100 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-11ef4ea945284c92873d0393a5085c2f
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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